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2‐Benzoyl Thienothiazoles from Annulation of C−H Bonds in Acetophenone Oximes
Author(s) -
Pham Phuc H.,
Nguyen Khang X.,
Nguyen Ninh P.,
Pham Hoai T. B.,
Nguyen Tung T.,
Phan Nam T. S.
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000046
Subject(s) - chemistry , acetophenone , oxime , annulation , medicinal chemistry , halogen , methylene , alcohol , ketone , solvent , sulfur , organic chemistry , catalysis , alkyl
We report a method for coupling of acetophenone oxime acetates, C−H bonds α to ketones, and elemental sulfur. The reactions proceeded in the presence of Li 2 CO 3 (base) and DMSO (solvent) to afford 2‐benzoyl benzothienothiazoles. Functionalities including halogen, protected alcohol, and heterocycle groups were compatible with reaction conditions. Use of methylene C−H bonds in β‐keto esters is also viable. This marks a rare example for mild synthesis of S‐heterocycles from ketoxime acetates.